Hydrochloric Acid → 16-Cyanohexadecanoic acid

HRID 2174347Notes

Reaction equation

HRID 2174347 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[C-:20]#[N:21].[Na+].[Na+].[I-].Cl>O.CS(C)=O>[C:20]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])#[N:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 62039716-Bromohexadecanoic acid

Product 1

HCID 1904720516-Cyanohexadecanoic acidYield 72.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 16-bromohexadecanoic acid (16.61 g, 49.5 mmol), DMSO (150 ml), NaCN (12.5 g, 255 mmol), and NaI (1.92 g, 12.8 mmol) was stirred at 120° C. for 20 h. The mixture was allowed to cool to room temperature, and was then poured into a stirred mixture of water (1.7 l) and concentrated HCl (30 ml). Rinsing with water (100 ml). The resulting suspension was stirred at room temperature overnight. The product was filtered and washed with water (2×100 ml), and the solid was recrystallized twice from MeCN (90 ml and 50 ml). 10.1 g (72%) of 16-cyanohexadecanoic acid was obtained.

Workup

  1. temperatureto cool to room temperature
  2. washRinsing with water (100 ml)
  3. stirringThe resulting suspension was stirred at room temperature overnight
  4. filtrationThe product was filtered
  5. washwashed with water (2×100 ml)
  6. customthe solid was recrystallized twice from MeCN (90 ml and 50 ml)

Sources & evidence

ORD record
ord-f433f1ecae224476a8e1681951906a1e
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

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